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<h1><a href="https://archiveofourown.org/works/29160792">Jim and Michael’s Deal</a> by <a class='authorlink' href='https://archiveofourown.org/users/rcumm20/pseuds/rcumm20'>rcumm20</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Slutty Jim [1]</td></tr>

<tr><td><b>Category:</b></td><td>The Office (US)</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Sex, Bathroom Sex, Bottom Michael, Gay Sex, M/M, Smut, Top Jim</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2021-02-02</td></tr>

<tr><td><b>Updated:</b></td><td>2021-02-02</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-13 10:34:29</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>908</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/29160792</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/rcumm20/pseuds/rcumm20</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Jim is offered a deal by Michael that he just can’t refuse.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Jim Halpert/Michael Scott</td></tr>

<tr><td><b>Series:</b></td><td>Slutty Jim [1]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/2140644</td></tr>

<tr><td><b>Kudos:</b></td><td>25</td></tr>

</table>

<a name="section0001"><h2>Jim and Michael’s Deal</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>First writing so suggestions, criticism, or other comments are all welcome!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Michael breathed a long, steady breath out as he bent over and stared at the toilet where his and Jim’s work clothing laid. Jim was slipping on a condom with his right hand as he loosened up Michaels hole with his left thumb. </p><p>	“Wow Jim, I would’ve made this deal with you a long time ago if I knew you were so good at this,” Michael said.</p><p>	“I haven’t even started...” Jim replied, not surprised that this was Michael’s first time.</p><p>	“Oh. Umm I know... Uhh I’m just excited.”</p><p>	Jim was cool and relaxed, but Michael wasn’t making this easy. Jim was starting to regret this deal, but he thought about the pay raise again and he knew it was worth it. Have a couple of ‘private meetings’ with Michael in exchange for a promotion and a raise. It was a tough decision, but it was worth it in Jim’s eyes.</p><p>He told Michael to stand up and face towards him. Jim lifted him up and he wrapped his legs around Jim’s waist and his arms around Jim’s neck.</p><p>	“Ok Michael, are you ready? I’m putting it in now.” Jim said, making direct eye contact to make sure Michael was actually listening.</p><p>	“Okay, yeah, I’m ready Jim. Do it.”</p><p>	“Breathe Michael, breathe.”</p><p>	Jim lined his lengthy member up with Michael’s rear entrance and poked lightly before slowly entering.</p><p>Michael suddenly inhaled sharply. “AHH, too much, too big, too big.” He scrunched his face to cope with the foreign feeling, but then relaxed and started laughing.</p><p>	“What? Michael what happened?” Jim said as he carefully pulled out and set Michael down.</p><p>	“That’s what he said!” Michael wheezed out with his hands on his knees. “Get it!? Because... Because it’s... it’s too big,” he couldn’t speak with out giggling. </p><p>	Jim was worried about how this would play out considering he had barely even gotten the tip in. He habitually looked up to stare at the camera in disappointment, but looked back at Michael when his eyes found not a camera but a stall door</p><p>	“Do you really think this is the time for jokes. You were pinned up against a bathroom stall getting anally penetrated and you’re making jokes?” Jim said in a confused tone.</p><p>	“Yeah Jim, sex is the perfect time for sex jokes.” Michael chuckled as if it was obvious. Jim sighed and added, “Okay, how about we lean away from the jokes and focus a little bit more.” They both nodded to each other in agreement, but Michael was just a little bit disappointed that he wouldn’t be able to practice any more jokes. </p><p>	“Ok Michael, let’s try again. I’ll go a little slower this time.” Jim said, surprised he was still hard at all. He hoped this was worth the extra money and made a mental note to buy viagra for the next ‘meeting.’</p><p>	“Okay,” he said as he took another long breath. “I’m ready.”</p><p>	Michael was lifted up against the stall door again, and Jim jerked his cock quickly to get the blood pumping again. He flicked his head lightly against Michael’s somewhat hairy asshole and he slowly and carefully put pressure on the entrance. Michael kept a steady breathing pattern and tried his best to avoid gasping or manning to loud at Jim’s unbelievable length. Jim got farther in this time, but it wasn’t long before Michael let out a long, loud moan.</p><p>	“Oh god yes.”</p><p>	All of Michael’s thoughts melted away as Jim slowly receded and re-entered his ass. Little by little, Jim increased the speed of his pumps and they were going at it hard in no time. Michael moaned on and on, and Jim was starting to get concerned a co-worker might hear him so he covered Michaels mouth with one of his hands while gripping tightly to his bottom’s back. Michael took Jim’s hand and moved it down to his neck and Jim immediately went with it and began putting pressure on Michael’s throat, pushing him back against the stall door. This pleased both of them. </p><p>	Soon enough, Michael came without having to touch his dick and his cum shot up in between the men, most of it returning to his own chest. Jim was both surprised at how much Michael let out, and also pleased by the fact that he was the cause of his boss’s pleasure. Michael let out short, quiet moans now, each in time with Jim’s thrusts and the shaking of the stall. </p><p>	“I’m... I think I’m gonna cum Michael,” Jim said suddenly, his thick pumping veins visible on every extremity.</p><p>	He slid his long cock out of Michael, pushed the man down to his knees, ripped off his condom, and shoved his dick into the man’s mouth. Michael let Jim guide his head, and simply opened his mouth. He enjoyed in the sweet taste of Jim’s cock and the scent of his bushy pubes while it lasted. Michael felt pure bliss in this movement.</p><p>	It took only five pushes in Michael’s mouth, and then Jim shoved his cock so far it reached down to the bottom of Michael’s throat. Jim let go, his jizz flooding Michael’s throat and mouth. He smiled as his little hookup choked his seed down. Michael smiled back mischievously. </p><p>	Jim erased that mental note of his, surprised by how the interaction turned out. He enjoyed it more than he would like to admit  and even looked forward to their future encounters.</p>
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